It has been quite a journey, with two league titles and the Checkatrade Trophy to show for an exile that began in 2012 with relegation under Michael Appleton.
There have also been plenty of gutting lows during the long battle to return to the Championship – and not just restricted to awful owners and High Court battles.
So here’s a list of the 20 worst Pompey matches since leaving the Championship – in no particular order...
5. Pompey 3 Coventry 3 (August 20, 2019)
Pompey appeared to be cruising to a 3-1 victory over 10-man Coventry with 15 minutes remaining. Then it was 3-2 against nine men with 12 minutes left, prompting Kenny Jackett to replace Gareth Evans with defender Christian Burgess - a decision questioned still to this day. Ultimately, Michael Rose's 86th-minute goal earned an improbable point for the nine-man visitors and, in some supporters' eyes, Jackett never again regained their trust. Picture: Robin Jones/Digital South Photo: Robin Jones
6. Swindon 5 Pompey 0 (January 1, 2013)
Pompey headed to Swindon on the back of 12 matches without a victory in all competitions and under caretaker boss Guy Whittingham. Encouragingly, by the 60th minute the match was goalless - then Paolo Di Canio introduced James Collins off the bench. He subsequently scored a 12-minute hat-trick and finished with four goals overall as the Robins ran riot for the remainder of the game to inflict a 5-0 thumping. Picture: Sarah Standing Photo: Sarah Standing
7. Morecambe 1 Pompey 1 (February 2, 2016)
Pompey appeared set for a 1-0 victory at Morecambe thanks to Gareth Evans, with his goal putting them on track to boost their promotion challenge under Paul Cook. That was until Morecambe won a 94th-minute corner and, with goalkeeper Barry Roche joining the attack, he subsequently netted with a head to claim a dramatic point. It was a long trip home that Tuesday night. Picture: Joe Pepler Photo: Joe Pepler
8. Southend 3 Pompey 3 (February 16, 2019)
Former long-time League One leaders Pompey were worringly on the slide heading to Southend, yet found themselves 3-0 up after a blistering opening 31 minutes. However, they were undone by Simon Cox's hat-trick, including an 87th-minute leveller, as Kenny Jackett's men frustratingly let slip their lead and instead ended up with a dismal Roots Hall point. Picture: Joe Pepler Photo: Joe Pepler